Category: chlorides-buliding-blocks

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 14752-66-0, name is Sodium 4-chlorobenzenesulfinate, A new synthetic method of this compound is introduced below., Application In Synthesis of Sodium 4-chlorobenzenesulfinate

To the reactor was added 0.20 mmol of phenacetylene, 0.30 mmol of sodium p-chlorophenylsulfinate,0.40 mmol of ferric chloride hexahydrate, 2.0 mL of trifluoroethanol solvent. Heated to 120 C under a nitrogen atmosphere,After stirring for 3 h, the reaction was stopped, cooled to room temperature, extracted with dichloromethane, dried, and the solvent was removed by distillation under reduced pressure. The crude product was separated by column chromatography to give the desired product in 86% yield.

The synthetic route of 14752-66-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Hunan University; Yin, Shuangfeng; Ceng, Kui; Chen, Lang; Zhou, Yongbo; (8 pag.)CN106083669; (2016); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 51419-59-1, These common heterocyclic compound, 51419-59-1, name is p-Tolylmethanesulfonyl chloride, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

No. B1-152: N-(1?-Methyl-2?-oxo-1?,2?-dihydrospiro[cyclobutane-1,3?-indol]-5-yl)-1-(4-methylphenyl)methanesulfonamide (0136) (0137) In a round-bottom flask which had been dried by heating, and under argon, 1-methyl-1,3-dihydro-2H-indol-2-one (1.00 g, 7 mmol) and 1,3-dibromopropane (2.06 g, 10 mmol) were dissolved in abs. N,N-dimethylformamide, and the mixture was stirred at room temperature for 5 min. The reaction solution was then cooled to 0° C., and sodium hydride (0.82 g, 20 mmol, 60percent strength dispersion) was then added a little at a time. The resulting reaction mixture was stirred for about 2 h, methanol (4 ml) was then added and after a further 5 min sat. ammonium chloride solution (15 ml) and water (200 ml) were added. The aqueous phase was extracted intensively with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (360 mg, 29percent of theory). 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.52 (d, 1H), 7.27 (m, 1H), 7.09 (m, 1H), 6.77 (d, 1H), 3.20 (s, 3H), 2.67 (m, 2H), 2.33 (m, 4H). 1?-Methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (360 mg, 1.92 mmol) was added to conc. acetic acid (5 ml), and fuming nitric acid (0.21 ml, 5.06 mmol) was then added carefully. The resulting reaction mixture was stirred at room temperature for 2 h and then diluted with ice-water. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 1?-methyl-5?-nitrospiro[cyclobutane-1,3?-indol]-2?(1?H)-one (380 mg, 85percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 8.38 (d, 1H), 8.26 (dd, 1H), 6.86 (d, 1H), 3.25 (s, 3H), 2.70 (m, 2H), 2.42 (m, 4H). In the next step, 1?-methyl-5-nitrospiro[cyclobutane-1,3?-indol]-2?(1?H)-one (450 mg, 1.55 mmol) and tin(II) chloride dihydrate (1.40 g, 6.20 mmol) were added together to abs. ethanol and stirred under argon at a temperature of 80° C. for 5 h. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 using aqueous NaOH. The aqueous phase was then repeatedly extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave 5?-amino-1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (230 mg, 66percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 6.98 (d, 1H), 6.62 (m, 2H), 3.14 (s, 3H), 2.64 (m, 2H), 2.38-2.20 (m, 4H). Under argon, 5?-amino-1?-methylspiro[cyclobutane-1,3?-indol]-2?(1?H)-one (150 mg, 0.79 mmol) and (4-methylphenyl)methanesulfonyl chloride (156 mg, 0.76 mmol) were dissolved in abs. acetonitrile (5 ml) in a round-bottom flask which had been dried by heating, pyridine (0.11 ml, 1.38 mmol) and dimethyl sulfoxide (0.03 ml, 0.42 mmol) were then added and the mixture was stirred at room temperature for 6 h. The reaction mixture was then concentrated under reduced pressure, water, dil. hydrochloric acid and dichloromethane were added to the residue that remained and the aqueous phase was extracted repeatedly with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification of the resulting crude product by column chromatography (gradient ethyl acetate/heptane) gave N-(1?-methyl-2?-oxo-1?,2?-dihydrospiro[cyclobutane-1,3?-indol]-5?-yl)-1-(4-methylphenyl)methanesulfonamide (118 mg, 46percent of theory) as a colorless solid. 1H-NMR (400 MHz, CDCl3 delta, ppm) 7.29 (m, 3H), 7.16 (d, 1H), 6.96 (br. s, 1H, NH), 6.61 (d, 1H), 4.30 (s, 2H), 3.13 (s, 3H), 2.62 (m, 2H), 2.33 (s, 3H), 2.32-2.17 (m, 4H).

The synthetic route of 51419-59-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BAYER CROPSCIENCE AKTIENGESELLSCHAFT; FRACKENPOHL, Jens; BOJACK, GUIDO; HELMKE, HENDRIK; LEHR, STEFAN; MUELLER, THOMAS; WILLMS, LOTHAR; DITTGEN, JAN; SCHMUTZLER, DIRK; BICKERS, UDO; STREK, HARRY; BALTZ, RACHEL; (88 pag.)US2016/237035; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Application of 1996-29-8, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 1996-29-8, name is 1-Bromo-4-chloro-2-fluorobenzene belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

To a stirred solution of 1-bromo-4-chloro-2-fluorobenzene (5 g, 23.87mmol) in tetrahydrofuran (40 mL) was cooled to -78 C was added LDA, 2M inTHF/heptane/ethylbenzene (14.92 mL, 29.8 mmol) dropwise and the reaction mixture was stirred at this temperature for 30 mm. The solution was allowed to warm to -20 C and stirred for 30 mm. The reaction was cooled to -78 C and trimethyl borate (3.47 mL, 31.0 mmol) dissolved in THF (5 mL) was addeddropwise and the reaction mixture was warmed to -20 C and stirred for 1 h. The reaction mixture was cooled to -78 C and peracetic acid (16 mL, 84 mmol) was added dropwise and the mixture allowed to warm to rt and stirred for 12 h. The reaction mixture was cooled to 0 C and quenched with 5% aqueous ammonium chloride and extracted with ethyl acetate (2X50 mL). The combined organiclayers were washed with brine (50 mL). The organic layer was dried over sodium sulphate and concentrated under reduced pressure to yield 3-bromo-6-chloro-2- fluorophenol (4.99 g, 18.25 mmol, 76% yield) as yellow oil. LCMS (ESI) m/e 225.1 [(M+H), calcd for C6H4BrC1FO 224.9]; LC/MS retention time (method G): tR = 0.87 mm.

The synthetic route of 1-Bromo-4-chloro-2-fluorobenzene has been constantly updated, and we look forward to future research findings.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; VRUDHULA, Vivekananda M.; PAN, Senliang; RAJAMANI, Ramkumar; MACOR, John E.; BRONSON, Joanne J.; DZIERBA, Carolyn Diane; NARA, Susheel Jethanand; KARATHOLUVHU, Maheswaran Sivasamban; WO2015/38112; (2015); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 626-43-7, name is 3,5-Dichloroaniline, A new synthetic method of this compound is introduced below., COA of Formula: C6H5Cl2N

3,5-dichloroanilme ( 1 eq), ethyl 2-bromoacetate (3eq) and NaOAc (3 eq) in EtOH was refiuxed overnight. The solvent was removed under reduced pressure and the residue was extracted with DCM. The orgamc layer was dried over sodium sulfate, concentrated in vacuum, and the residue was purified through Hash chromatography on silica gel eluted with EA-Hexane to give ethyl 2-((3,5-dichlorophenyl)amino)acetate.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; UNIVERSITY OF WASHINGTON; BUCKNER, Frederick, S.; ALVAREZ, Ximena, Barros; FAN, Erkang; GILLESPIE, John, Robert; HOL, Wilhelmus, G.J.; HUANG, Wenlin; KOH, Cho, Yeow; RANADE, Ranae, M.; SHIBATA, Sayaka; VERLINDE, Christophe, L.M.; ZHANG, Zhongsheng; (249 pag.)WO2016/29146; (2016); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 2687-12-9, name is Cinnamyl chloride, belongs to chlorides-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 2687-12-9, Computed Properties of C9H9Cl

General procedure: A representative procedure of skeleton 4 is as follows: K2CO3 (400 mg, 2.9 mmol) was added to a solution of 3 (1.0 mmol) in acetone (10 mL) at rt. The reaction mixture was stirred at rt for 10 min. Cinnamyl chloride (1.05 mmol) was added to the reaction mixture at rt. The reaction mixture was stirred at reflux for 8 h. The reaction mixture was cooled to rt, concentrated, and extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried, filtered, and evaporated to afford crude product under reduced pressure. Purification on silica gel (hexanes/EtOAc=6:1 to 1:1) afforded 4.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Cinnamyl chloride, and friends who are interested can also refer to it.

Reference:
Article; Chang, Meng-Yang; Lu, Yi-Ju; Cheng, Yu-Chieh; Tetrahedron; vol. 71; 8; (2015); p. 1192 – 1201;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

These common heterocyclic compound, 2533-69-9, name is Methyl 2,2,2-trichloroacetimidate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route. Quality Control of Methyl 2,2,2-trichloroacetimidate

Example 7> Preparation of 1H-benzoimidazole-2-carboxylic acid[6-(2-methyl-pyridine-3-yloxy)-pyridine-3-yl]-amide 1,2-phenylenediamine (1 g, 9.25 mmol) was dissolved in acetic acid (30 ), methyltrichloroacetimidate (1.26 , 10.18 mmol) was added to the solution at 0 , and then the mixture was stirred at room temperature. After the reaction was completed, the product was washed, filtered, and dried to obtain 2-trichloromethyl-1H-benzoimidazole.

The synthetic route of Methyl 2,2,2-trichloroacetimidate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; KOREA RESERACH INSTITUTE OF CHEMICAL TECHNOLOGY; WO2009/125923; (2009); A2;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Reference of 4090-55-5, These common heterocyclic compound, 4090-55-5, name is 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

In a 250 ml three-necked flask equipped with a stirrer, a thermometer and a reflux condenser, 50 ml of acetonitrile, 2-aminothiazole (0.11 mol, 11.0 g) and triethylamine (0.3 mol, 30.3 g) were added and stirred to mix well. Further, a solution of neopentyl glycolphosphoryl chloride (0.1 mol, 18.5 g) in acetonitrile (100 ml) was added dropwise with stirring at 3 C, and the system remains clear and transparent. After the solution was added dropwise, the system was allowed to react at 3 C for 3 h, and then heated to 70 C for 8 h. After completion of the reaction, the solvent was removed by rotary evaporation to obtain a reddish brown solid, which was washed three times with chloroform to remove the triethylamine hydrochloride. After drying, a one-component intumescent flame retardant (PAZ) for epoxy resin was obtained. The yield was 95%.

Statistics shows that 2-Chloro-5,5-dimethyl-1,3,2-dioxaphosphorinane 2-oxide is playing an increasingly important role. we look forward to future research findings about 4090-55-5.

Reference:
Patent; Fujian Normal University; Jian Rongkun; Ai Yuanfang; Xia Long; Pang Fuqu; (9 pag.)CN109400649; (2019); A;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Electric Literature of 39989-43-0, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 39989-43-0, name is 3,5-Dichlorobenzylamine belongs to chlorides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

EXAMPLE 30 2-[3,5-Dichlorobenzylamino]-4-[benzimidazol-1-yl]pyrimidine 2-Methanesulfonyl-4-[benzimidazol-1-yl]pyrimidine was reacted with 3,5-dichlorobenzylamine according to the procedure described in EXAMPLE 1, Step C to afford the title compound. Mass Spectrum (EI): m/e 370.3 (M+1). 1H NMR (500 MHz, CDCl3): delta 8.58 (s, 1H); 8.45 (d, J=5.5 Hz, 1H); 7.98 (br s, 1H); 7.86 (m, 1H); 7.38 (m, 2H); 7.31 (s, 2H); 6.89 (d, J=5.5 Hz, 1H); 5.88 (br s, 1H); 4.72 (d, J=6.4 Hz, 2H).

The synthetic route of 3,5-Dichlorobenzylamine has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Merck & Co., Inc.; US6498165; (2002); B1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

Related Products of 89794-02-5, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 89794-02-5 name is 4-Bromo-2-chlorotoluene, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

l-(3-Chloro-4-methylphenyl)-3-phenylpiperazine (compound of type 14, Figure 11): 2-phenyl- piperazine (0.13 g, 0.80 mmol), 2-Cl-4-Br-toluene (0.10 ml, 0.76 mmol), Pd2dba3 (0.07 g, 0.08 mmol), BINAP (0.048 g, 0.08 mmol) and OtBu (0.13 g, 1.14 mmol) were stirred in toluene (2 mL) at 80C. Aqueous work up, dichloromethane extraction and removal of volatiles was followed by flash chromatography separation using ethyl acetate gradient ( 10-60%) in hexanes to afford 0.13 g (56%) of l-(3–Chloro-4-methylphenyl)-3 -phenylpiperazine 14. 1H – NMR (CDC13, 400 MHz, delta ppm) 7.46-7.44 (m, 2H), 7.39-7.29 (m, 3H), 7.08 (d, / = 8.4 Hz, 1H), 6.91 (d, / = 2.8 Hz, 1H), 6.75 (dd, / = 8.8, 2.8 Hz, 1H), 3.96 (dd, / = 10.4, 2.8 Hz, 1H), 3.57-3.54 (m, 2H), 3.24 (dt, / = 11.6, 3.2 Hz, 1H), 2.86 (td, / = 11.6, 3.2 Hz, 1H), 2.68 (t, / = 11.2 Hz, 1H), 2.27 (s, 3H).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4-Bromo-2-chlorotoluene, and friends who are interested can also refer to it.

Reference:
Patent; SHIFA BIOMEDICAL CORPORATION; ABDEL-MEGUID, Sherin, Salaheldin; ABOU-GHARBIA, Magid; BLASS, Benjamin; CHILDERS, Wayne; ELSHOURBAGY, Nabil; GHIDU, Victor; MARTINEZ, Rogelio; MEYERS, Harold; MOUSA, Shaker, A.; WO2014/150395; (2014); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics

13526-66-4, name is 3-Bromo-6-chloroimidazo[1,2-b]pyridazine, belongs to chlorides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. Safety of 3-Bromo-6-chloroimidazo[1,2-b]pyridazine

a) ierf-Butyl 4-[(3-bromoimidazo[1 ,2-b]pyridazin-6-yl)amino]piperidine-1 -carboxylateA solution of 3-bromo-6-chloroimidazo[1 ,2-b]pyridazine (3.00 g, 12.9 mmol 1.0 eq) in NMP (15 ml_) was treated with te/f-butyl 4-aminopiperidine-1 -carboxylate (5.10 g, 25.8 mmol, 2.0 eq), DIPEA (5.60 mL, 32.3 mmol, 2.5 eq) and heated at 130C for 5 h. The reaction mixture was diluted with DCM (100 mL) and washed with de-ionised water (3 x 150 mL). The separated organic was concentrated in vacuo and column chromatography (10-80% EtOAc/pet ether) gave a brown solid (3.01 g, 59%); 1H NMR (400 MHz, DMSO-d6) delta ppm 7.71 (d, J=9.6 Hz, 1 H), 7.48 (s, 1 H), 7.10 (d, br, J=7.3 Hz, 1H), 6.68 (d, J=10.1 Hz, 1H), 3.87-3.82 (m, 3H), 3.02-2.93 (m, 2H), 2.02-1.98 (m, 2H), 1.41 (s, 9H), 1.40-1.31 (m, 2H); m/z (ES+APCI)+: 396/398 [M+H]+.

The synthetic route of 13526-66-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MEDICAL RESEARCH COUNCIL TECHNOLOGY; OSBORNE, Simon; CHAPMAN, Timothy; WALLACE, Claire; WO2012/127212; (2012); A1;,
Chloride – Wikipedia,
Chlorides – an overview | ScienceDirect Topics